US3954658A - Oil-in-water emulsion and emulsifying or solubilizing composition therefor - Google Patents
Oil-in-water emulsion and emulsifying or solubilizing composition therefor Download PDFInfo
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- US3954658A US3954658A US05/601,971 US60197175A US3954658A US 3954658 A US3954658 A US 3954658A US 60197175 A US60197175 A US 60197175A US 3954658 A US3954658 A US 3954658A
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- United States
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- oil
- weight
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- ingredient
- fatty acid
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- Expired - Lifetime
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- 239000000203 mixture Substances 0.000 title claims abstract description 47
- 230000001804 emulsifying effect Effects 0.000 title claims abstract description 18
- 230000003381 solubilizing effect Effects 0.000 title claims description 5
- 239000007764 o/w emulsion Substances 0.000 title claims 2
- 239000003995 emulsifying agent Substances 0.000 claims abstract description 47
- -1 polyoxyethylene Polymers 0.000 claims abstract description 27
- 239000000194 fatty acid Substances 0.000 claims abstract description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 9
- 229930195729 fatty acid Natural products 0.000 claims abstract description 9
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 8
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims abstract description 8
- 125000002252 acyl group Chemical group 0.000 claims abstract description 7
- 239000002202 Polyethylene glycol Substances 0.000 claims abstract description 6
- 229920001223 polyethylene glycol Polymers 0.000 claims abstract description 6
- 239000004094 surface-active agent Substances 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 239000000839 emulsion Substances 0.000 claims description 41
- 239000003921 oil Substances 0.000 claims description 21
- 235000019198 oils Nutrition 0.000 claims description 21
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 16
- 239000010696 ester oil Substances 0.000 claims description 15
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 14
- 239000008158 vegetable oil Substances 0.000 claims description 14
- 239000004615 ingredient Substances 0.000 claims description 12
- 239000010495 camellia oil Substances 0.000 claims description 11
- 239000004006 olive oil Substances 0.000 claims description 10
- 235000008390 olive oil Nutrition 0.000 claims description 10
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 9
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 9
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 9
- 239000005642 Oleic acid Substances 0.000 claims description 9
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 9
- BCKXLBQYZLBQEK-KVVVOXFISA-M Sodium oleate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC([O-])=O BCKXLBQYZLBQEK-KVVVOXFISA-M 0.000 claims description 9
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 6
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 235000019482 Palm oil Nutrition 0.000 claims description 2
- 235000019484 Rapeseed oil Nutrition 0.000 claims description 2
- 235000019485 Safflower oil Nutrition 0.000 claims description 2
- 239000002385 cottonseed oil Substances 0.000 claims description 2
- 235000012343 cottonseed oil Nutrition 0.000 claims description 2
- XJNUECKWDBNFJV-UHFFFAOYSA-N hexadecyl 2-ethylhexanoate Chemical compound CCCCCCCCCCCCCCCCOC(=O)C(CC)CCCC XJNUECKWDBNFJV-UHFFFAOYSA-N 0.000 claims description 2
- 239000002540 palm oil Substances 0.000 claims description 2
- 235000005713 safflower oil Nutrition 0.000 claims description 2
- 239000003813 safflower oil Substances 0.000 claims description 2
- TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 claims 2
- 235000021360 Myristic acid Nutrition 0.000 claims 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims 2
- BTURAGWYSMTVOW-UHFFFAOYSA-M sodium dodecanoate Chemical compound [Na+].CCCCCCCCCCCC([O-])=O BTURAGWYSMTVOW-UHFFFAOYSA-M 0.000 claims 2
- 229940082004 sodium laurate Drugs 0.000 claims 2
- 239000005639 Lauric acid Substances 0.000 claims 1
- 229940045845 sodium myristate Drugs 0.000 claims 1
- JUQGWKYSEXPRGL-UHFFFAOYSA-M sodium;tetradecanoate Chemical compound [Na+].CCCCCCCCCCCCCC([O-])=O JUQGWKYSEXPRGL-UHFFFAOYSA-M 0.000 claims 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 abstract description 46
- 239000002904 solvent Substances 0.000 abstract description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 34
- 238000004945 emulsification Methods 0.000 description 15
- 230000032050 esterification Effects 0.000 description 14
- 238000005886 esterification reaction Methods 0.000 description 14
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 12
- FFJCNSLCJOQHKM-CLFAGFIQSA-N (z)-1-[(z)-octadec-9-enoxy]octadec-9-ene Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCCCCCCC\C=C/CCCCCCCC FFJCNSLCJOQHKM-CLFAGFIQSA-N 0.000 description 12
- 235000011187 glycerol Nutrition 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 9
- 229940049964 oleate Drugs 0.000 description 8
- 229940114926 stearate Drugs 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 239000002537 cosmetic Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 5
- 239000006071 cream Substances 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 5
- FDCJDKXCCYFOCV-UHFFFAOYSA-N 1-hexadecoxyhexadecane Chemical compound CCCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCC FDCJDKXCCYFOCV-UHFFFAOYSA-N 0.000 description 4
- HBXWUCXDUUJDRB-UHFFFAOYSA-N 1-octadecoxyoctadecane Chemical compound CCCCCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCCCC HBXWUCXDUUJDRB-UHFFFAOYSA-N 0.000 description 4
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- GSGDTSDELPUTKU-UHFFFAOYSA-N nonoxybenzene Chemical compound CCCCCCCCCOC1=CC=CC=C1 GSGDTSDELPUTKU-UHFFFAOYSA-N 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 238000005191 phase separation Methods 0.000 description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000000600 sorbitol Substances 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 3
- 229940070765 laurate Drugs 0.000 description 3
- 239000006210 lotion Substances 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229940096992 potassium oleate Drugs 0.000 description 3
- MLICVSDCCDDWMD-KVVVOXFISA-M potassium;(z)-octadec-9-enoate Chemical compound [K+].CCCCCCCC\C=C/CCCCCCCC([O-])=O MLICVSDCCDDWMD-KVVVOXFISA-M 0.000 description 3
- 235000003441 saturated fatty acids Nutrition 0.000 description 3
- 150000004671 saturated fatty acids Chemical class 0.000 description 3
- RYOCYIVCDUMYAL-VFQQELCFSA-N (2r,3r,4r,5s)-hexane-1,2,3,4,5,6-hexol;oxirane Chemical compound C1CO1.OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO RYOCYIVCDUMYAL-VFQQELCFSA-N 0.000 description 2
- MUHFRORXWCGZGE-KTKRTIGZSA-N 2-hydroxyethyl (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCO MUHFRORXWCGZGE-KTKRTIGZSA-N 0.000 description 2
- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 description 2
- 239000010775 animal oil Substances 0.000 description 2
- 235000013871 bee wax Nutrition 0.000 description 2
- 229940092738 beeswax Drugs 0.000 description 2
- 239000012166 beeswax Substances 0.000 description 2
- 239000003974 emollient agent Substances 0.000 description 2
- 229940095098 glycol oleate Drugs 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- YEGNTQBFSQBGJT-UHFFFAOYSA-N 2-heptylundecan-1-ol Chemical compound CCCCCCCCCC(CO)CCCCCCC YEGNTQBFSQBGJT-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000008278 cosmetic cream Substances 0.000 description 1
- 239000008341 cosmetic lotion Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229940105132 myristate Drugs 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229940114930 potassium stearate Drugs 0.000 description 1
- ANBFRLKBEIFNQU-UHFFFAOYSA-M potassium;octadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCCCC([O-])=O ANBFRLKBEIFNQU-UHFFFAOYSA-M 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 229940032094 squalane Drugs 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/06—Emulsions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
- A61K8/361—Carboxylic acids having more than seven carbon atoms in an unbroken chain; Salts or anhydrides thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4993—Derivatives containing from 2 to 10 oxyalkylene groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/017—Mixtures of compounds
- C09K23/018—Mixtures of two or more different organic oxygen-containing compounds
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
- Y10S516/06—Protein or carboxylic compound containing
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/905—Agent composition per se for colloid system making or stabilizing, e.g. foaming, emulsifying, dispersing, or gelling
- Y10S516/917—The agent contains organic compound containing oxygen
- Y10S516/918—The compound contains carboxylic acid ester group
Definitions
- This invention relates to an emulsifying or solubilizing agent composition which is highly effective for emulsifying and solubilizing liquid vegetable oils and highly polar synthetic ester oils, the emulsification or solubilization of which has heretofore been regarded as being very difficult.
- non-ionic surface active agents such as polyoxyethylene sorbitan-fatty acid esters, sorbitan-fatty acid esters, glycerol-fatty acid esters, polyethylene glycol-fatty acid esters and polyoxyethylenealkyl esters, but also a great variety of non-ionic, anionic, cationic and amphoteric surface active agents.
- these emulsifiers have a good emulsifying activity to mineral oils composed of hydrocarbons and the like and animal oils such as squalane, and they provide stable emulsions of these oils.
- these surface active agents can scarcely emulsify liquid vegetable oils composed of triglycerides full of aliphatic hydrocarbon groups having unsaturated bonds (hereinafter referred to merely as “vegetable oils”), such as camellia oil and olive oil, or esters having at least one branched alkyl group, which are synthesized from a branched or linear higher fatty acid and a branched or linear higher alcohol (hereinafter referred to merely as "synthetic ester oils”), and stable emulsions of these vegetable oils or synthetic ester oils have not been provided.
- vegetable oils composed of triglycerides full of aliphatic hydrocarbon groups having unsaturated bonds
- vegetable oils such as camellia oil and olive oil
- esters having at least one branched alkyl group which are synthesized from a branched or linear higher fatty acid and a branched or linear higher alcohol
- synthetic ester oils stable emulsions of these vegetable oils or synthetic ester oils have not been provided.
- an emulsifying or solubilizing agent capable of readily emulsifying or solubilizing the aforesaid vegetable oils or synthetic ester oils to provide stable emulsions thereof.
- a composition formed by incorporating specific amounts of a fatty acid alkali metal salt, a fatty acid and an oleic acid ester of a polyethylene glycol into a polyoxyethylene sorbitol-fatty acid ester type surface active agent.
- an emulsifying or solubilizing agent composition comprising 58 to 95% by weight of a polyoxyethylene sorbitol-unsaturated fatty acid ester (hereinafter referred to as "component (I)") having the formula (A) ##EQU2## wherein the sum of n1 + n2 + n3 + n4 + n5 + n6 is from 10 to 60, and on the average up to 3 of the X's are hydrogen and the balance of the X's are linear unsaturated acyl groups having 18 carbon atoms,
- component (II) an alkali metal salt of a linear saturated or olefinically unsaturated fatty acid having 12 to 18 carbon atoms
- component (III) a linear saturated or olefinically unsaturated fatty acid having 12 to 18 carbon atoms
- component (IV) a C 18 linear unsaturated fatty acid ester of a polyethylene glycol having an average molecular weight of 150 to 2,000
- the aforesaid types of vegetable oils and synthetic ester oils which are highly polar emollient oils and have heretofore been regarded as being difficult to emulsify, can easily be emulsified or solubilized, and good, stable and ideal emulsions of these oils can be obtained.
- These vegetable oils are liquid vegetable oils composed of triglycerides containing many unsaturated aliphatic hydrocarbon groups, such as camellia oil, olive oil, safflower oil, rapeseed oil, palm oil and cotton seed oil, and the synthetic ester oils are esters having at least one branched alkyl group, which are synthesized from branched or linear higher fatty acids and branched or linear higher alcohols.
- synthetic ester oil there can be mentioned, for example, 2-heptylundecyl isostearate, glyceroltris-2-ethylhexanoate, hexadecyl-2-ethylhexanoate, hexadecyl isostearate and hexadecyl isotridecanoate.
- These vegetable oils and synthetic ester oils are especially useful for cosmetics, and by the use of the composition of this invention, it is possible to employ these oils in the emulsified or solubilized state in cosmetics.
- composition of this invention exhibits an excellent emulsifying effect not only to these vegetable oils and synthetic ester oils, but also to mineral oils and animal oils which can also be emulsified by conventional emulsifiers.
- the polyoxyethylene sorbitol-unsaturated fatty acid ester used as the component (I) in this invention is obtained by partially or fully esterifying a sorbitol-ethylene oxide adduct with an unsaturated fatty acid having 18 carbon atoms, such as oleic acid.
- an unsaturated fatty acid having 18 carbon atoms such as oleic acid.
- the 6 hydroxyl groups of said adduct from 3 to 6 of such groups, on the average, are esterified.
- from 3 to 6 of the X's are acyl groups and the remaining X's are hydrogen.
- the degree of esterification When a compound having a lower degree of esterification outside the above range is employed, the emulsifying effect is diminished and good emulsions cannot be obtained. Further, the stability is reduced. Unsaturated fatty acids having 18 carbon atoms, preferably oleic acid and linoleic acid, are employed for this esterification.
- RCO-- wherein R is an olefinically unsaturated acyclic unbranched hydrocarbon radical having 17 carbon atoms and having from one to 4 double bonds in the hydrocarbon chain.
- saturated fatty acids such as stearic acid and palmitic acid are employed for esterifying the sorbitolethylene oxide adduct, the emulsifying effect of compositions containing such esters is very low. Further, since esters of such saturated fatty acids are solid at room temperature, the use of such saturated fatty acids for esterification purposes is not acceptable.
- the compound of formula (A) is synthesized by customary methods by dissolving sorbitol in a solvent such as xylene, adding thereto ethylene oxide in the presence of a basic catalyst to cause an addition reaction between sorbitol and ethylene oxide, adding to that adduct an unsaturated fatty acid in an amount of from 3 to 6 moles per mole of the resulting adduct, carrying out esterification at 220° to 240°C and decolorizing and purifying the final reaction product.
- a solvent such as xylene
- composition of this invention consists essentially of 58 to 95% by weight of the component (I), 0.5 to 1.0% by weight of the component (II), 2.5 to 6.0% by weight of the component (III) and 2 to 35% by weight of the component (IV).
- Compositions outside this range do not have a satisfactory emulsifying or solubilizing effect to the aforesaid vegetable oils and synthetic ester oils, and because of the poor stability of any emulsion that may be formed, the resulting emulsions are destroyed in a short time when they are allowed to stand still, resulting in phase separation.
- the emulsifying or solubilizing agent composition of this invention is especially valuable when used for cosmetics, but it can be utilized as an emulsifier or solubilizing agent in various fields where these oils are employed, namely in the arts of foodstuffs, fiber-treating oils, detergents, metal-processing oils and the like.
- the composition of this invention is employed in an amount of from 5 to 100 percent by weight, based on the weight of the oil component, to form oil-in-water emulsions.
- a mixture of 20 parts of the oil component, 5 parts of the emulsifying agent composition and 75 parts of deionized water was emulsified at a temperature of 70°C, employing an agitating propeller rotation rate of 600 rpm, according to the phase inversion emulsification method.
- the emulsifiability and stability of each emulsion were evaluated based on the following standards:
- the state of the as-prepared emulsion was examined and observed with the naked eye and by a microscope, and the emulsifiability was evaluated by the following rating scale:
- A bluish white emulsion of fine particles, the average particle size as measured by using the microscope being smaller than 1 ⁇
- the invention provides mostly A grade emulsions, but some acceptable B grade emulsions can be obtained also.
- the emulsion comprising 75 parts of the aqueous phase and 25 parts of the oil phase was allowed to stand still at 25°C for 7 days, and the ratios of separation of the emulsion into oil and aqueous phases were determined.
- the stability was calculated from these separation ratios according to the following formula:
- an emulsion which retains a completely emulsified state has a stability point of 0 (zero) and an emulsion which has been separated completely into an oil phase and an aqueous phase has a stability point of 20.
- the stability point the better is the emulsion.
- the average degree of esterification of the component (I) (the number of acyl groups as X in the formula (A)) is within the range of from 3 to 6, an excellent emulsifying effect is attained and an emulsion of good stability is obtained.
- the average degree of esterification is 2 or lower, the emulsifying effect is low, and the stability of the resulting emulsion is bad and significant phase separation occurs.
- Tests of the emulsification of camellia oil were conducted by using various emulsifiers (compositions) as shown in Table 2.
- the compounding proportions were 20 parts of camellia oil, 5 parts of emulsifier composition and 75 parts of deionized water.
- the test methods and evaluation methods were the same as described in Example 1 except that the stability was determined after the passage of 1 day and 1 week, respectively, and the emulsion was allowed to stand at 5°, 20° or 40°C.
- Example 2 In the same manner as described in Example 2, the emulsification tests were conducted by using a mixture of 20 parts of the above synthetic ester oil, 5 parts of an emulsifier (composition) and 74 parts of deionized water. The results are shown in Table 5.
- the degree of esterification of component (I) was 4.5
- the component (II) was sodium oleate
- the component (III) was oleic acid
- the average molecular weight of component (IV) was 600. It will be noted that in comparative products 2-1 to 2-8, the proportions of the ingredients are outside the ranges of proportions of the ingredients according to the invention.
- Comparative products 3-1 to 3-7, 4-1 to 4-5, 5-1 to 5-6, 6, 7-1 and 7-2 consisted of the components as listed in the Tables.
- the mark (*) indicates that the emulsifiability was low, although because the viscosity of the emulsion was so high that no phase separation occurred.
- An emulsifying agent composition comprising the following components was prepared:
- This emulsifying agent composition was a yellowish brown liquid having a specific gravity (d 4 20 ) of 0.962, a viscosity of 172 cps as measured at 20°C, a saponification value of 118.8 and an HLB value of 8.2.
- Components (1) and components (2) were separately heated and melted, and both the melts were mixed under vigorous agitation to form an emulsion. While the emulsion was being cooled, components (3) were added and dispersed uniformly to obtain a cream. This cream had a very good emulsion state.
- This emulsifying agent composition was a yellowish brown liquid having a specific gravity (d 4 20 ) of 1.03, a viscosity of 321 cop as measured at 20°C, a saponification value of 82.8 and an HLB value of 11.6.
- a milky lotion having the following composition was prepared in the same manner as described in Example 6.
- the resulting milky lotion had a good emulsion state, and was very stable even after passage of a long time.
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Abstract
An emulsifying or solubilizing agent composition comprising 58 to 95% by weight of a surface active agent of the polyoxyethylene sorbitol-unsaturated fatty acid ester type having the formula ##EQU1## wherein the sum of n1 + n2 + n3 + n4 + n5 + n6 is from 10 to 60, and on the average, up to 3 of the X's are hydrogen and the balance of the X's are linear unsaturated acyl groups having 18 carbon atoms,
0.5 to 1.0% by weight of an alkali metal salt of a linear fatty acid having 12 to 18 carbon atoms, 2.5 to 6.0% by weight of a linear fatty acid, and 2 to 35% by weight of C18 linear unsaturated fatty acid ester of a polyethylene glycol having an average molecular weight of 150 to 2,000.
Description
BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates to an emulsifying or solubilizing agent composition which is highly effective for emulsifying and solubilizing liquid vegetable oils and highly polar synthetic ester oils, the emulsification or solubilization of which has heretofore been regarded as being very difficult.
2. Description of the Prior Art
As emulsifiers for cosmetics, there have heretofore been used not only non-ionic surface active agents such as polyoxyethylene sorbitan-fatty acid esters, sorbitan-fatty acid esters, glycerol-fatty acid esters, polyethylene glycol-fatty acid esters and polyoxyethylenealkyl esters, but also a great variety of non-ionic, anionic, cationic and amphoteric surface active agents. In general, these emulsifiers have a good emulsifying activity to mineral oils composed of hydrocarbons and the like and animal oils such as squalane, and they provide stable emulsions of these oils. However, these surface active agents can scarcely emulsify liquid vegetable oils composed of triglycerides full of aliphatic hydrocarbon groups having unsaturated bonds (hereinafter referred to merely as "vegetable oils"), such as camellia oil and olive oil, or esters having at least one branched alkyl group, which are synthesized from a branched or linear higher fatty acid and a branched or linear higher alcohol (hereinafter referred to merely as "synthetic ester oils"), and stable emulsions of these vegetable oils or synthetic ester oils have not been provided.
We have discovered an emulsifying or solubilizing agent capable of readily emulsifying or solubilizing the aforesaid vegetable oils or synthetic ester oils to provide stable emulsions thereof. According to our invention, there is provided a composition formed by incorporating specific amounts of a fatty acid alkali metal salt, a fatty acid and an oleic acid ester of a polyethylene glycol into a polyoxyethylene sorbitol-fatty acid ester type surface active agent. More specifically, in accordance with this invention, there is provided an emulsifying or solubilizing agent composition comprising 58 to 95% by weight of a polyoxyethylene sorbitol-unsaturated fatty acid ester (hereinafter referred to as "component (I)") having the formula (A) ##EQU2## wherein the sum of n1 + n2 + n3 + n4 + n5 + n6 is from 10 to 60, and on the average up to 3 of the X's are hydrogen and the balance of the X's are linear unsaturated acyl groups having 18 carbon atoms,
0.5 to 1.0% by weight of an alkali metal salt of a linear saturated or olefinically unsaturated fatty acid having 12 to 18 carbon atoms (hereinafter referred to as "component (II)"), 2.5 to 6.0% by weight of a linear saturated or olefinically unsaturated fatty acid having 12 to 18 carbon atoms (hereinafter referred to as "component (III)"), and 2 to 35% by weight of a C18 linear unsaturated fatty acid ester of a polyethylene glycol having an average molecular weight of 150 to 2,000 (hereinafter referred to as "component (IV)").
When the above composition is used as an emulsifying or solubilizing agent, the aforesaid types of vegetable oils and synthetic ester oils, which are highly polar emollient oils and have heretofore been regarded as being difficult to emulsify, can easily be emulsified or solubilized, and good, stable and ideal emulsions of these oils can be obtained. These vegetable oils are liquid vegetable oils composed of triglycerides containing many unsaturated aliphatic hydrocarbon groups, such as camellia oil, olive oil, safflower oil, rapeseed oil, palm oil and cotton seed oil, and the synthetic ester oils are esters having at least one branched alkyl group, which are synthesized from branched or linear higher fatty acids and branched or linear higher alcohols. As such synthetic ester oil, there can be mentioned, for example, 2-heptylundecyl isostearate, glyceroltris-2-ethylhexanoate, hexadecyl-2-ethylhexanoate, hexadecyl isostearate and hexadecyl isotridecanoate. These vegetable oils and synthetic ester oils are especially useful for cosmetics, and by the use of the composition of this invention, it is possible to employ these oils in the emulsified or solubilized state in cosmetics. More specifically, it is possible to incorporate such emulsified or solubilized vegetable oils or synthetic ester oils into various cosmetic creams and lotions such as sun creams and hair creams, and to obtain cosmetics which are superior to conventional cosmetics composed mainly of mineral oils, with respect to their mild emollient effects. The composition of this invention exhibits an excellent emulsifying effect not only to these vegetable oils and synthetic ester oils, but also to mineral oils and animal oils which can also be emulsified by conventional emulsifiers.
As will be seen from the above formula (A), the polyoxyethylene sorbitol-unsaturated fatty acid ester used as the component (I) in this invention is obtained by partially or fully esterifying a sorbitol-ethylene oxide adduct with an unsaturated fatty acid having 18 carbon atoms, such as oleic acid. Among the 6 hydroxyl groups of said adduct, from 3 to 6 of such groups, on the average, are esterified. In other words, in the formula (A), from 3 to 6 of the X's are acyl groups and the remaining X's are hydrogen. (Hereinafter, the number of such acyl groups is referred to as "the degree of esterification".) When a compound having a lower degree of esterification outside the above range is employed, the emulsifying effect is diminished and good emulsions cannot be obtained. Further, the stability is reduced. Unsaturated fatty acids having 18 carbon atoms, preferably oleic acid and linoleic acid, are employed for this esterification. Thus, from 3 to 6 of the X's of the Formula (A) compound have the formula RCO--, wherein R is an olefinically unsaturated acyclic unbranched hydrocarbon radical having 17 carbon atoms and having from one to 4 double bonds in the hydrocarbon chain. If saturated fatty acids such as stearic acid and palmitic acid are employed for esterifying the sorbitolethylene oxide adduct, the emulsifying effect of compositions containing such esters is very low. Further, since esters of such saturated fatty acids are solid at room temperature, the use of such saturated fatty acids for esterification purposes is not acceptable. The compound of formula (A) is synthesized by customary methods by dissolving sorbitol in a solvent such as xylene, adding thereto ethylene oxide in the presence of a basic catalyst to cause an addition reaction between sorbitol and ethylene oxide, adding to that adduct an unsaturated fatty acid in an amount of from 3 to 6 moles per mole of the resulting adduct, carrying out esterification at 220° to 240°C and decolorizing and purifying the final reaction product.
It is critial that the composition of this invention consists essentially of 58 to 95% by weight of the component (I), 0.5 to 1.0% by weight of the component (II), 2.5 to 6.0% by weight of the component (III) and 2 to 35% by weight of the component (IV). Compositions outside this range do not have a satisfactory emulsifying or solubilizing effect to the aforesaid vegetable oils and synthetic ester oils, and because of the poor stability of any emulsion that may be formed, the resulting emulsions are destroyed in a short time when they are allowed to stand still, resulting in phase separation.
In view of the properties of the oils to which the composition of this invention is applied, the emulsifying or solubilizing agent composition of this invention is especially valuable when used for cosmetics, but it can be utilized as an emulsifier or solubilizing agent in various fields where these oils are employed, namely in the arts of foodstuffs, fiber-treating oils, detergents, metal-processing oils and the like. In general, the composition of this invention is employed in an amount of from 5 to 100 percent by weight, based on the weight of the oil component, to form oil-in-water emulsions.
This invention will now be further described in detail by reference to the following illustrative Examples. In the following examples, all references to "%" and "parts" are by weight, unless otherwise indicated.
Tests of the emulsification of various oils were conducted by using emulsifiers having the following compositions:
Ingredient Compositon (%) of Emulsifier
______________________________________
a b c
Component (I)* 60.0 70.0 80.0
Component (II) (sodium oleate)
0.7 0.7 0.7
Component (III) (oleic acid)
5.0 5.0 5.0
Component (IV) (average
34.3 24.3 14.3
molecular weight = 600)
______________________________________
*As the component (I), there were employed 7 kinds of compounds differing
in the degree of esterification, ranging from a compound in which the
degree of esterification with oleic acid was 0 to a compound in which 6
hydroxyl groups were completely esterified. In each of these compounds th
average mole number of the added ethylene oxide was 30.
Test Procedures
A mixture of 20 parts of the oil component, 5 parts of the emulsifying agent composition and 75 parts of deionized water was emulsified at a temperature of 70°C, employing an agitating propeller rotation rate of 600 rpm, according to the phase inversion emulsification method. The emulsifiability and stability of each emulsion were evaluated based on the following standards:
1. Emulsifiability:
The state of the as-prepared emulsion was examined and observed with the naked eye and by a microscope, and the emulsifiability was evaluated by the following rating scale:
A: bluish white emulsion of fine particles, the average particle size as measured by using the microscope being smaller than 1 μ
B: milky white emulsion, the average particle size as measured by using the microscope being 1 to 5 μ
C: opaque crude emulsion, the average particle size as measured by using the microscope being larger than 5 μ
In general, the invention provides mostly A grade emulsions, but some acceptable B grade emulsions can be obtained also.
2. Stability:
The emulsion comprising 75 parts of the aqueous phase and 25 parts of the oil phase was allowed to stand still at 25°C for 7 days, and the ratios of separation of the emulsion into oil and aqueous phases were determined. The stability was calculated from these separation ratios according to the following formula:
Stability Point =
(Ratio (vol %) of Separation of Oil Phase +
Ratio (vol %) of Separation of aqueous phase)
× 1/10
For example, an emulsion which retains a completely emulsified state (no phase separation) has a stability point of 0 (zero) and an emulsion which has been separated completely into an oil phase and an aqueous phase has a stability point of 20. Thus, the lowere the stability point, the better is the emulsion.
The results are shown in Table 1.
Table 1
__________________________________________________________________________
Emulsifier Emulsifiability
(Degree of Esterification in Component (I)
Composition
Oil Stability
(number of acyl groups in formula
__________________________________________________________________________
(A))
0 1 2 3 4 5 6
a Olive Oil Emulsifiability
C C B A A A B
Stability
20.0
15.0
12.0
0.0 0.0 0.0 2.5
Camellia Oil
Emulsifiability
C C B A A A B
Stability
20.0
15.7
9.7
0.0 0.0 0.0 2.5
2-Heptylundecyl
Emulsifiability
C C B A A A A
Isostearate
Stability
18.3
15.3
4.3
0.0 0.0 0.0 0.0
b Olive Oil Emulsifiability
C C C B A A B
Stability
20.0
15.0
12.5
4.3 0.0 0.0 2.5
Camellia Oil
Emulsifiability
C C C A A A A
Stability
20.0
15.3
10.8
0.0 0.0 0.0 0.0
2-Heptylundecyl
Emulsifiability
C C C A A A A
Isostearate
Stability
20.0
17.8
4.5
0.0 0.0 0.0 0.0
c Olive Oil Emulsifiability
C C C B A A A
Stability
20.0
20.0
15.7
10.0
0.0 0.0 0.0
Camellia Oil
Emulsifiability
C C C A A A A
Stability
20.0
18.7
13.0
0.0 0.0 0.0 0.0
2-Heptylundecyl
Emulsifiability
C C C A A A A
Isostearate
Stability
20.0
19.5
8.3
0.0 0.0 0.0 0.0
__________________________________________________________________________
As is seen from the above results, in the composition of this invention, when the average degree of esterification of the component (I) (the number of acyl groups as X in the formula (A)) is within the range of from 3 to 6, an excellent emulsifying effect is attained and an emulsion of good stability is obtained. On the other hand, when the average degree of esterification is 2 or lower, the emulsifying effect is low, and the stability of the resulting emulsion is bad and significant phase separation occurs.
Tests of the emulsification of camellia oil were conducted by using various emulsifiers (compositions) as shown in Table 2. The compounding proportions were 20 parts of camellia oil, 5 parts of emulsifier composition and 75 parts of deionized water. The test methods and evaluation methods were the same as described in Example 1 except that the stability was determined after the passage of 1 day and 1 week, respectively, and the emulsion was allowed to stand at 5°, 20° or 40°C.
The results are shown in Table 2.
In the same manner as described in Example 2, emulsification tests were conducted by using a mixture of 20 parts of olive oil, 5 parts of an emulsifier (composition) and 75 parts of deionized water.
The results are shown in Table 3.
In the same manner as described in Example 2, the emulsification tests were conducted by using a mixture of 20 parts of a synthetic ester oil obtained by esterification of 2-heptylundecanol with isostearic acid, 5 parts of an emulsifier (composition) and 75 parts of deionized water. The results are shown in Table 4.
In the same manner as described in Example 2, the emulsification tests were conducted by using a mixture of 20 parts of the above synthetic ester oil, 5 parts of an emulsifier (composition) and 74 parts of deionized water. The results are shown in Table 5.
In each of the following Tables 2-5, the emulsifier products of the invention tested had the following characteristics:
Degree
of Average
Products
n1+n2+ Esteri- Molecular
of the n3+n4+ fication Weight of
Invention
n5+n6 of (I) II III (IV)
______________________________________
1-1 10 3.0 sodium lauric 163
laurate
acid
1-2 20 4.0 sodium lauric 313
laurate
acid
1-3 30 4.5 sodium oleic 458
oleate acid
1-4 30 4.5 sodium myristic
458
laurate
acid
1-5 40 4.5 sodium myristic
603
myristate
acid
1-6 60 5.0 sodium oleic 898
oleate acid
______________________________________
In the comparative products 2-1 to 2-8, the degree of esterification of component (I) was 4.5, the component (II) was sodium oleate, the component (III) was oleic acid and the average molecular weight of component (IV) was 600. It will be noted that in comparative products 2-1 to 2-8, the proportions of the ingredients are outside the ranges of proportions of the ingredients according to the invention.
Comparative products 3-1 to 3-7, 4-1 to 4-5, 5-1 to 5-6, 6, 7-1 and 7-2 consisted of the components as listed in the Tables.
In the Tables, the mark (*) indicates that the emulsifiability was low, although because the viscosity of the emulsion was so high that no phase separation occurred.
Table 2
__________________________________________________________________________
Results of Tests of Emulsification of Camellia Oil
Composition
Invention
Proportion (wt.%) HLB Emulsion
Emulsifiers
(I) (II) (III) (IV) Type
__________________________________________________________________________
1-1 73.5 0.72 4.8 20.98 8.2 O/W
1-2 85.0 0.65 4.5 9.85 9.2 O/W
1-3 72.0 0.90 3.7 23.40 10.6 O/W
1-4 70.0 0.70 4.2 25.10 10.3 O/W
1-5 60.5 0.92 4.4 34.18 11.6 O/W
1-6 75.0 0.58 3.7 20.72 13.2 O/W
Comparative
Emulsifiers
2-1 70.0 0 5.0 25.0 10.3 O/W
2-2 69.8 0.2 0 30.0 10.3 O/W
2-3 72.0 0.2 1.4 26.4 10.3 O/W
2-4 40.2 0.6 4.2 55.0 10.1 O/W
2-5 20.0 0.6 2.4 77.0 10.0 O/W
2-6 100.0 0 0 0 10.4 O/W
2-7 0 0 0 100 9.9 O/W
2-8 0 0 100 0 -- O/W
3-1 POE (20) sorbitan mono- 8.0 O/W
3-2 oleate/sorbitan 9.0 O/W
3-3 monooleate 10.0 O/W
3-4 11.0 O/W
3-5 12.0 O/W
3-6 13.0 O/W
3-7 POE (20) sorbitan 11.0 O/W
trioleate
4-1 POE (8) stearate/glycerol
8.0 O/W
4-2 monostearate 9.0 O/W
4-3 10.0 O/W
4-4 11.0 O/W
4-5 POE (50) stearate/glycerol
12.0 O/W
monostearate
4-6 " 13.0 O/W
5-1 POE (5) oleyl ether 8.8 O/W
5-2 POE (5) nonylphenyl ether
9.2 O/W
5-3 POE (6) oleyl ether 10.0 O/W
5-4 POE (6) stearyl ether 9.4 O/W
5-5 POE (7) cetyl ether 10.7 O/W
5-6 POE (9) oleyl ether 12.1 O/W
6 polyoxyethylene-polyoxy-
propylene condensate -- O/W
7-1 sodium oleate -- O/W
7-2 potassium stearate -- O/W
__________________________________________________________________________
Stability of Formed Emulsion
Invention
Emulsi-
after one day's
after one week's
Emulsifiers
fiability
standing standing
__________________________________________________________________________
5°C
20°C
40°C
5°C
20°C
40°C
1-1 A 0 0 0 0 0 0
1-2 A 0 0 0 0 0 0
1-3 A 0 0 0 0 0 0
1-4 A 0 0 0 0 0 0
1-5 A 0 0 0 0 0 0
1-6 B 0 0 0 4.5 5.2 5.2
Comparative
Emulsifiers
2-1 C 2.5 2.5 3.5 9.3 9.7 10.0
2-2 B 0.2 0.5 0.5 12.5 12.5 12.5
2-3 A 0 0 0 8.0 8.0 8.3
2-4 C 9.7 9.5 9.7 12.5 12.5 12.5
2-5 C 8.0 8.5 8.5 10.0 9.7 10.0
2-6 C 12.3 12.7 15.0 18.5 18.5 18.5
2-7 C 8.5 10.0 12.5 10.0 12.5 13.4
2-8 C 20.0 20.0 20.0 20.0 20.0 20.0
3-1 C 8.5 8.5 8.5 8.7 8.7 9.3
3-2 C 8.0 8.0 8.5 8.0 8.0 8.7
3-3 C 8.5 8.5 8.7 9.3 9.3 9.3
3-4 C 8.7 8.7 8.7 9.3 9.3 9.3
3-5 C 9.3 9.3 9.3 9.7 9.8 14.6
3-6 C 9.3 9.3 9.3 9.5 9.7 14.9
3-7 C 8.0 8.0 8.5 8.7 9.3 9.3
4-1 C 0* 0* 0* 0* 0* 0*
4-2 C 0* 0* 0* 0* 0* 0*
4-3 C 0* 0* 2.5 0* 0* 5.3
4-4 C 0* 0* 8.0 0* 0* 9.3
4-5 C 0* 5.3 8.0 0* 8.7 8.0
4-6 C 0* 8.0 8.8 0* 8.7 9.1
5-1 C 12.5 12.5 15.0 12.5 15.0 15.0
5-2 C 17.0 17.5 18.5 20.0 20.0 20.0
5-3 C 8.0 8.7 8.7 8.0 9.3 9.3
5-4 C 8.0 8.7 8.7 8.0 9.3 9.3
5-5 C 6.6 7.3 10.0 6.7 7.3 10.0
5-6 C 10.0 17.5 19.5 10.0 18.0 20.0
6 C 9.3 9.3 9.3 17.5 12.5 9.3
7-1 B 5.2 5.7 5.7 9.3 9.7 9.7
7-2 B 5.0 5.7 5.7 10.0 8.5 10.0
__________________________________________________________________________
Table 3
__________________________________________________________________________
Results of Tests of Emulsification of Olive Oil
Composition
Invention
Proportion (wt.%) HLB Emulsion
Emulsifiers
(I) (II) (III) (IV) Type
__________________________________________________________________________
1-2 85.0 0.65 4.5 9.85 9.2 O/W
1-3 72.0 0.90 3.7 23.40 10.6 O/W
1-4 70.0 0.70 4.2 25.10 10.3 O/W
1-5 60.5 0.92 4.4 34.18 11.6 O/W
Comparative
Emulsifiers
2-1 70.0 0 5.0 25.0 10.3 O/W
2-2 69.8 0.2 0 30.0 10.3 O/W
2-3 72.0 0.2 1.4 26.4 10.3 O/W
2-4 40.2 0.6 4.2 55.0 10.1 O/W
2-5 20.0 0.6 2.4 77.0 10.0 O/W
2-6 100.0 0 0 0 10.4 O/W
2-7 0 0 0 100 9.9 O/W
2-8 0 0 100 0 -- O/W
3-1 POE (20) sorbitan mono- 8.0 O/W
3-2 oleate/sorbitan 9.0 O/W
3-3 monooleate 10.0 O/W
3-4 11.0 O/W
3-5 12.0 O/W
3-6 13.0 O/W
3-7 POE (20) sorbitan 11.0 O/W
trioleate
4-1 POE (8) stearate/glycerol
8.0 O/W
4-2 monostearate 9.0 O/W
4-3 10.0 O/W
4-4 11.0 O/W
4-5 POE (50) stearate/glycerol
12.0 O/W
monostearate
4-6 " 13.0 O/W
5-1 POE (5) oleyl ether 8.8 O/W
5-2 POE (5) nonylphenyl ether
9.2 O/W
5-3 POE (6) oleyl ether 10.0 O/W
5-4 cetyl (6) stearyl ether 9.4 O/W
5-5 POE (7) cetyl ether 10.7 O/W
5-6 POE (9) oleyl ether 12.1 O/W
6 polyoxyethylene-polyoxy-
propylene condensate -- O/W
7-1 sodium oleate -- O/W
7-2 potassium oleate -- O/W
__________________________________________________________________________
Stability of Formed Emulsion
Invention
Emulsi-
after one day's
after one week's
Emulsifiers
fiability
standing standing
__________________________________________________________________________
5°C
20°C
40°C
5°C
20°C
40°C
1-2 B 0 0 0 0 0 0
1-3 A 0 0 0 0 0 0
1-4 A 0 0 0 0 0 0
1-5 A 0 0 0 0 0 0
Comparative
Emulsifiers
2-1 C 9.5 9.7 9.7 15.0 15.0 15.0
2-2 B 2.5 2.7 3.2 10.0 10.0 10.0
2-3 B 0.2 0.2 3.0 10.0 10.0 10.0
2-4 C 7.3 9.5 9.5 9.3 9.5 10.0
2-5 C 9.5 9.5 9.5 9.7 10.0 13.0
2-6 C 9.5 9.5 9.5 15.0 15.0 15.0
2-7 C 10.0 10.0 15.0 15.0 15.0 15.0
2-8 C 20.0 20.0 20.0 20.0 20.0 20.0
3-1 C 9.0 9.0 9.0 9.3 9.3 9.3
3-2 C 9.5 9.5 9.5 9.5 9.5 10.0
3-3 C 9.5 9.5 10.0 9.7 10.0 10.0
3-4 C 9.5 9.5 10.0 10.0 10.0 10.0
3-5 C 8.5 9.5 9.5 9.5 10.0 10.0
3-6 C 10.0 9.5 9.5 10.0 9.5 10.3
3-7 C 10.0 10.0 12.5 10.0 10.0 15.0
4-1 C 0* 0* 0* 0* 0* 0*
4-2 C 0* 0* 0* 0* 0* 0*
4-3 C 0* 0* 0* 0* 0* 0*
4-4 C 0* 0.6 8.0 0* 0.6 8.0
4-5 C 0* 1.0 8.0 0* 8.3 8.0
4-6 C 0* 1.0 9.5 0* 8.7 9.5
5-1 C 8.0 8.7 9.5 8.0 8.7 9.5
5-2 C 10.0 10.0 10.0 15.0 15.0 20.0
5-3 C 8.0 9.5 9.5 8.7 10.0 10.0
5-4 C 0* 0* 0* 0* 0* 0*
5-5 C 6.7 6.7 9.5 6.7 7.5 10.0
5-6 C 9.5 9.5 9.5 10.0 10.0 10.0
6 C 9.5 10.0 10.0 10.0 15.0 15.0
7-1 B 0.2 0.2 0.5 10.0 10.0 10.0
7-2 B 0.2 0.2 0.5 10.0 10.0 10.0
__________________________________________________________________________
Table 4
__________________________________________________________________________
Results of Tests of Emulsification of 2-Heptylundecyl Isostearate
Composition
Invention
Proportion (wt.%) HLB Emulsion
Emulsifiers
(I) (II) (III) (IV) Type
__________________________________________________________________________
1-1 73.5 0.72 4.8 20.98 8.2 O/W
1-2 85.0 0.65 4.5 9.85 9.2 O/W
1-3 72.0 0.90 3.7 23.40 10.6 O/W
1-4 70.0 0.70 4.2 25.10 10.3 O/W
1-5 60.5 0.92 4.4 34.18 11.6 O/W
1-6 75.0 0.58 3.7 20.72 13.2 O/W
Comparative
Emulsifiers
2-1 70.0 0 5.0 25.0 10.3 O/W
2-2 69.8 0.2 0 30.0 10.3 O/W
2-3 72.0 0.2 1.4 26.4 10.3 O/W
2-4 40.2 0.6 4.2 55.0 10.1 O/W
2-5 20.0 0.6 2.4 77.0 10.0 O/W
2-6 100.0 0 0 0 10.4 O/W
2-7 0 0 0 100 9.9 O/W
2-8 0 0 100 0 -- O/W
3-1 POE (20) sorbitan mono- 8.0 O/W
3-2 oleate/sorbitan 9.0 O/W
3-3 monooleate 10.0 O/W
3-4 11.0 O/W
3-5 12.0 O/W
3-6 13.0 O/W
3-7 POE (20) sorbitan 11.0 O/W
trioleate
4-1 POE (8) stearate/glycerol
8.0 O/W
4-2 monostearate 9.0 O/W
4-3 10.0 O/W
4-4 11.0 O/W
4-5 POE (50) stearate/glycerol
12.0 O/W
monostearate
4-6 " 13.0 O/W
5-1 POE (5) oleyl ether 8.8 O/W
5-2 POE (5) nonylphenyl ether
9.2 O/W
5-3 POE (6) oleyl ether 10.0 O/W
5-4 POE (6) stearyl ether 9.4 O/W
5-5 POE (7) cetyl ether 10.7 O/W
5-6 POE (9) oleyl ether 12.1 O/W
6 polyoxyethylene-polyoxy-
-- O/W
propylene
7-1 sodium oleate -- O/W
7-2 potassium oleate -- O/W
__________________________________________________________________________
Stability of Formed Emulsion
Invention
Emulsi-
after one day's
after one week's
Emulsifiers
fiability
standing standing
__________________________________________________________________________
5°C
20°C
40°C
5°C
20°C
40°C
1-1 B 0 0 0 0.2 0.3 0.5
1-2 A 0 0 0 0 0 0
1-3 A 0 0 0 0 0 0
1-4 A 0 0 0 0 0 0
1-5 A 0 0 0 0 0 0
1-6 B 0 0 0 0 0 0
Comparative
Emulsifiers
2-1 C 3.5 4.7 5.5 6.7 9.3 9.3
2-2 C 4.5 5.0 6.0 8.5 8.0 8.5
2-3 B 0.2 0.2 0.3 8.7 8.7 9.3
2-4 B 2.2 2.5 2.0 8.7 9.0 9.3
2-5 C 8.3 8.3 8.7 10.0 10.2 15.0
2-6 C 8.7 9.0 9.3 10.0 10.0 10.0
2-7 C 12.5 12.5 14.0 13.8 14.2 15.0
2-8 C 20.0 20.0 20.0 20.0 20.0 20.0
3-1 C 0* 0* 0* 0* 0* 0.1
3-2 B 0 0 0 0.1 0.1 0.6
3-3 A 0 0 0 0.2 0.2 0.6
3-4 C 0 0 0 8.9 8.9 9.3
3-5 C 8.7 9.9 10.4 10.4 10.4 10.7
3-6 C 8.9 8.9 8.9 10.4 10.7 10.7
3-7 C 0 0 0 0.2 0.6 0.7
4-1 C 0* 0* 0* 0* 0* 0*
4-2 C 0* 0* 0* 0* 0* 0*
4-3 C 0* 0* 0* 0* 0* 0*
4-4 C 0* 0* 0* 0* 0.7 2.1
4-5 C 0* 0* 0* 1.1 2.1 1.1
4-6 C 0* 0* 0* 4.7 5.4 8.1
5-1 C 8.1 9.5 9.7 9.7 9.5 9.7
5-2 C 8.7 12.5 13.5 14.5 14.5 15.0
5-3 C 0 0 0 4.5 5.4 9.1
5-4 C 0 0 0 8.7 9.3 9.3
5-5 C 6.7 8.0 8.7 6.7 8.1 8.9
5-6 C 7.3 9.1 10.0 7.3 9.3 10.1
6 C 10.0 12.5 14.5 17.0 17.5 17.5
7-1 C 6.2 4.0 10.0 9.3 8.0 12.5
7-2 C 5.7 4.2 10.0 9.7 8.5 12.5
__________________________________________________________________________
Table 5
__________________________________________________________________________
Results of Tests of Emulsification of Glycerol Tris-2-ethyl-hexanoate
Composition
Invention
Proportion (wt.%) HLB Emulsion
Emulsifiers
(I) (II) (III) (IV) Type
__________________________________________________________________________
1-1 73.5 0.72 4.8 20.98 8.2 O/W
1-2 85.0 0.65 4.5 9.85 9.2 O/W
1-3 72.0 0.90 3.7 23.40 10.6 O/W
1-4 70.0 0.70 4.2 25.10 10.3 O/W
1-5 60.5 0.92 4.4 34.18 11.6 O/W
1-6 75.0 0.58 3.7 20.72 13.2 O/W
Comparative
Emulsifiers
2-1 70.0 0 5.0 25.0 10.3 O/W
2-2 69.8 0.2 0 30.0 10.3 O/W
2-3 72.0 0.2 1.4 26.4 10.3 O/W
2-4 4.2 0.6 4.2 55.0 10.1 O/W
2-5 20.0 0.6 2.4 77.0 10.0 O/W
2-6 100.0 0 0 0 10.4 O/W
2-7 0 0 0 100 9.9 O/W
2-8 0 0 100 0 -- O/W
3-1 POE (20) sorbitan mono- 8.0 O/W
3-2 oleate/sorbitan 9.0 O/W
3-3 monooleate 10.0 O/W
3-4 11.0 O/W
3-5 12.0 O/W
3-6 13.0 O/W
3-7 POE (20) sorbitan 11.0 O/W
trioleate
4-1 POE (8) stearate/glycerol
8.0 O/W
4-2 monostearate 9.0 O/W
4-3 10.0 O/W
4-4 11.0 O/W
4-5 POE (50) stearate/glycerol
12.0 O/W
monostearate
4-6 " 13.0 O/W
5-1 POE (5) oleyl ether 8.8 O/W
5-2 POE (5) nonylphenyl ether
9.2 O/W
5-3 POE (6) oleyl ether 10.0 O/W
5-4 POE (6) stearyl ether 9.4 O/W
5-5 POE (7) cetyl ether 10.7 O/W
5-6 POE (9) oleyl ether 12.1 O/W
6 polyoxyethylene-polyoxy-
-- O/W
propylene condensate
7-1 sodium oleate -- O/W
7-2 potassium oleate -- O/W
__________________________________________________________________________
Stability of Formed Emulsion
Invention
Emulsi-
after one day's
after one week's
Emulsifiers
fiability
standing standing
__________________________________________________________________________
5°C
20°C
40°C
5°C
20°C
40°C
1-1 A 0 0 0 0 0 0
1-2 A 0 0 0 0 0 0
1-3 A 0 0 0 0 0 0
1-4 A 0 0 0 0 0 0
1-5 A 0 0 0 0 0 0
1-6 A 0 0 0 0 0.2 2.1
Comparative
Emulsifiers
2-1 C 4.5 4.7 4.7 8.5 9.2 9.5
2-2 C 4.5 4.9 5.3 8.0 9.7 10.0
2-3 B 0.2 0.2 0.2 0.8 1.0 1.0
2-4 C 8.0 8.7 8.9 9.3 9.3 9.5
2-5 C 9.3 9.5 9.5 9.7 10.0 12.0
2-6 C 7.7 8.0 8.7 8.7 9.3 10.0
2-7 C 8.7 9.5 12.5 12.5 14.7 15.0
2-8 C 20.0 20.0 20.0 20.0 20.0 20.0
3-1 A 0 0 0 0.2 0.2 0.2
3-2 B 0 0 0 0.2 0.2 0.2
3-3 C 0 0 0 0.2 0.2 0.2
3-4 C 0 0 0 0.2 5.4 10.0
3-5 C 0 0 8.5 9.7 9.6 9.3
3-6 C 0 2.5 8.5 8.4 9.3 8.9
3-7 C 0 9.7 9.7 9.3 9.7 10.0
4-1 C 0* 0* 0* 0* 0* 0*
4-2 C 0* 0* 0* 0* 0* 0*
4-3 C 0* 0* 0* 0* 0* 0*
4-4 C 0* 8.5 9.5 0* 8.7 9.3
4-5 C 0* 8.5 9.5 0* 8.7 9.7
4-6 C 0* 8.5 8.5 0* 10.0 9.6
5-1 C 8.7 9.5 9.7 8.7 10.0 10.0
5-2 C 12.5 13.5 12.0 14.3 20.0 20.0
5-3 C 6.7 8.0 6.7 6.0 8.3 7.3
5-4 C 0* 0* 0* 0.8 1.0 2.5
5-5 C 6.7 8.3 9.0 6.7 8.3 9.6
5-6 C 0 0 0 2.0 2.0 2.7
6 C 10.0 10.5 12.0 10.0 10.5 12.0
7-1 B 0 0.2 0.2 0.4 2.0 2.1
7-2 B 0 0.2 0.2 0.4 2.0 2.7
__________________________________________________________________________
As is seen from the results obtained in Examples 2 to 5, although vegetable oils or synthetic ester oils cannot be emulsified at all or can be emulsified only insufficiently by conventional known emulsifiers, they can easily be emulsified by the emulsifying agent composition of this invention and good emulsions having an excellent stability can be obtained. It is also seen that even if the same components as in this invention are used, if the proportion of these components is outside the ranges specified in this invention, no satisfactory emulsifying effect can be attained and the stability of the resulting emulsion is poor.
An emulsifying agent composition comprising the following components was prepared:
(I) polyoxyethylene (P=10) sorbitol
73.5%
oleate (average degree of ester-
ification = 3.0)
(II) sodium oleate 0.72%
(III) oleic acid 4.8%
(IV) polyethylene glycol oleate
20.98%
(average molecular weight = 200)
This emulsifying agent composition was a yellowish brown liquid having a specific gravity (d4 20) of 0.962, a viscosity of 172 cps as measured at 20°C, a saponification value of 118.8 and an HLB value of 8.2.
by using this emulsifying agent composition, an O/W type cream having the following composition was prepared:
(1) camellia oil 25 parts
bees wax 5 parts
paraffin wax 5 parts
vaseline 7 parts
emulsifying agent compo-
6 parts
sition
(2) glycerin 5 parts
water 47 parts
(3) perfume, preservative
suitable amounts
Components (1) and components (2) were separately heated and melted, and both the melts were mixed under vigorous agitation to form an emulsion. While the emulsion was being cooled, components (3) were added and dispersed uniformly to obtain a cream. This cream had a very good emulsion state.
An emulsifying agent having the following components was prepared:
(1) polyoxyethylene (P=40) sorbitol oleate
60.5%
(average degree of esterification = 4.5)
(II) sodium oleate 0.92%
(III) oleic acid 4.4%
(IV) polyethylene glycol oleate
34.18%
(average molecular weight = 800)
This emulsifying agent composition was a yellowish brown liquid having a specific gravity (d4 20) of 1.03, a viscosity of 321 cop as measured at 20°C, a saponification value of 82.8 and an HLB value of 11.6.
By using this emulsifying agent composition, a milky lotion having the following composition was prepared in the same manner as described in Example 6.
______________________________________
(1) olive oil 30 parts
bees wax 2 parts
paraffin wax 2 parts
cetyl alcohol 1 part
emulsifying agent composition
5 parts
(2) glycerin 5 parts
water 55 parts
(3) perfume, preservatives
______________________________________
The resulting milky lotion had a good emulsion state, and was very stable even after passage of a long time.
Claims (10)
1. An emulsifying or solubilizing composition, consisting essentially of
I. from 58 to 95 percent by weight of a surface active agent having the formula ##EQU3## wherein the sum of n1 to n6 is from 10 to 60 and, on the average, up to 3 of the X's are hydrogen and the balance of the X's are linear unsaturated acyl groups having 18 carbon atoms,
Ii. from 0.5 to 1.0 percent by weight of an alkali metal salt of a linear fatty acid having 12 to 18 carbon atoms,
Iii. from 2.5 to 6.0 percent by weight of a linear fatty acid having 12 to 18 carbon atoms, and
Iv. from 2 to 35 percent by weight of a C18 linear unsaturated fatty acid ester of polyethylene glycol having an average molecular weight of 150 to 2000.
2. A composition as claimed in claim 1 in which ingredient II is sodium oleate and ingredient III is oleic acid.
3. A composition as claimed in claim 1 in which ingredient II is sodium laurate and ingredient III is lauric acid.
4. A composition as claimed in claim 1 in which ingredient II is sodium laurate and ingredient III is myristic acid.
5. A composition as claimed in claim 1 in which ingredient II is sodium myristate and ingredient III is myristic acid.
6. A composition as claimed in claim 1, containing from about 60 to 80 percent by weight of ingredient I.
7. An oil-in-water emulsion containing as an emulsifier for the oil phase, from 5 to 100 percent by weight, based on the weight of the oil components, of a composition as claimed in claim 1.
8. An emulsion as claimed in claim 7, in which said oil component consists of a liquid vegetable oil consisting essentially of triglycides containing several unsaturated aliphatic hydrocarbon groups or synthetic ester oils having at least one branched alkyl group obtained by reacting a branched or linear higher fatty acid with a branched or linear higher alcohol.
9. An emulsion as claimed in claim 7 in which the oil component is selected from the group consisting of camellia oil, olive oil, safflower oil, rapeseed oil, palm oil and cotton seed oil.
10. An emulsion as claimed in claim 7 in which the oil component is selected from the group consisting of 2-heptylundecyl isostearate, glycerol-tris-2-ethylhexanoate, hexadecyl-2-ethylhexanoate, hexadecyl isostearate and hexadecyl isotridecanoate.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JA49-91086 | 1974-08-08 | ||
| JP49091086A JPS5118989A (en) | 1974-08-08 | 1974-08-08 | Nyuka mataha kayokazaisoseibutsu |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3954658A true US3954658A (en) | 1976-05-04 |
Family
ID=14016697
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US05/601,971 Expired - Lifetime US3954658A (en) | 1974-08-08 | 1975-08-05 | Oil-in-water emulsion and emulsifying or solubilizing composition therefor |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US3954658A (en) |
| JP (1) | JPS5118989A (en) |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4097403A (en) * | 1976-02-05 | 1978-06-27 | Kao Soap Co., Ltd. | Oil-in-water emulsion and emulsifying or solubilizing agent composition useful therein |
| EP0007737A1 (en) * | 1978-07-31 | 1980-02-06 | Atlas Chemical Industries (U.K.) Ltd | An aqueous solution containing a surfactant and its uses in emulsification |
| FR2443873A1 (en) * | 1978-12-14 | 1980-07-11 | Kao Corp | NOVEL EMULSIFYING COMPOSITION FOR THE PRODUCTION AND STABILIZATION OF WATER-IN-OIL EMULSIONS |
| US4454113A (en) * | 1982-09-21 | 1984-06-12 | Scm Corporation | Stabilization of oil and water emulsions using polyglycerol esters of fatty acids |
| US4608057A (en) * | 1985-06-03 | 1986-08-26 | Texaco Inc. | Clear stable motor fuel composition |
| EP0399377A1 (en) * | 1989-05-19 | 1990-11-28 | Nihon Parkerizing Co., Ltd. | Cold rolling oil for steel sheet |
| US4996004A (en) * | 1982-08-14 | 1991-02-26 | Bayer Aktiengesellschaft | Preparation of pharmaceutical or cosmetic dispersions |
| US5059347A (en) * | 1989-03-17 | 1991-10-22 | Ciba-Geigy Corporation | Aqueous antioxident emulsions |
| US5116536A (en) * | 1982-08-14 | 1992-05-26 | Bayer Aktiengesellschaft | Preparation of pharmaceutical or cosmetic dispersions |
| US5192462A (en) * | 1989-03-21 | 1993-03-09 | Croda Inc. | Thickening agents for topical preparations |
| WO2005059042A3 (en) * | 2003-12-17 | 2005-11-03 | Ici Plc | Surfactant |
| CN101448873B (en) * | 2006-05-19 | 2012-07-18 | 陶氏康宁东丽株式会社 | Polyether and method for producing the same |
| US11547137B2 (en) * | 2015-03-10 | 2023-01-10 | Givaudan Sa | Topical flavouring compositions comprising oleic acid and sodium oleate |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57197204A (en) * | 1981-05-27 | 1982-12-03 | Shiseido Co Ltd | Emulsion cosmetic |
| JP5362179B2 (en) * | 2006-10-20 | 2013-12-11 | 日清オイリオグループ株式会社 | Polyoxyethylene sorbitol fatty acid ester and aqueous wax dispersion containing the same |
| JP7788083B2 (en) | 2020-12-28 | 2025-12-18 | 大日本印刷株式会社 | Organic device, mask group, mask, and method for manufacturing organic device |
| JP7788084B2 (en) | 2020-12-28 | 2025-12-18 | 大日本印刷株式会社 | Organic device, mask group, mask, and method for manufacturing organic device |
| KR20220169923A (en) | 2021-06-21 | 2022-12-28 | 다이니폰 인사츠 가부시키가이샤 | Manufacturing method of mask and mask |
| US20220406853A1 (en) | 2021-06-21 | 2022-12-22 | Dai Nippon Printing Co., Ltd. | Organic device, group of masks, mask, and manufacturing method for organic device |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1500670A (en) * | 1923-03-17 | 1924-07-08 | Groote Melvin De | Making dilute permanent turbid emulsions |
| US2269529A (en) * | 1940-06-15 | 1942-01-13 | Harry Bennett | Emulsifier and emulsion |
| US2786013A (en) * | 1953-07-06 | 1957-03-19 | Atlas Powder Co | Emulsifier compositions and insecticidal emulsions |
| US3634285A (en) * | 1969-03-24 | 1972-01-11 | Stauffer Wacker Silicone Corp | Silicone release emulsion |
| US3795627A (en) * | 1971-06-04 | 1974-03-05 | Ici America Inc | Stable liquid emulsifier compositions |
-
1974
- 1974-08-08 JP JP49091086A patent/JPS5118989A/en active Granted
-
1975
- 1975-08-05 US US05/601,971 patent/US3954658A/en not_active Expired - Lifetime
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1500670A (en) * | 1923-03-17 | 1924-07-08 | Groote Melvin De | Making dilute permanent turbid emulsions |
| US2269529A (en) * | 1940-06-15 | 1942-01-13 | Harry Bennett | Emulsifier and emulsion |
| US2786013A (en) * | 1953-07-06 | 1957-03-19 | Atlas Powder Co | Emulsifier compositions and insecticidal emulsions |
| US3634285A (en) * | 1969-03-24 | 1972-01-11 | Stauffer Wacker Silicone Corp | Silicone release emulsion |
| US3795627A (en) * | 1971-06-04 | 1974-03-05 | Ici America Inc | Stable liquid emulsifier compositions |
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4097403A (en) * | 1976-02-05 | 1978-06-27 | Kao Soap Co., Ltd. | Oil-in-water emulsion and emulsifying or solubilizing agent composition useful therein |
| EP0007737A1 (en) * | 1978-07-31 | 1980-02-06 | Atlas Chemical Industries (U.K.) Ltd | An aqueous solution containing a surfactant and its uses in emulsification |
| FR2443873A1 (en) * | 1978-12-14 | 1980-07-11 | Kao Corp | NOVEL EMULSIFYING COMPOSITION FOR THE PRODUCTION AND STABILIZATION OF WATER-IN-OIL EMULSIONS |
| US4312777A (en) * | 1978-12-14 | 1982-01-26 | Kao Soap Co., Ltd. | Emulsifier composition |
| US5116536A (en) * | 1982-08-14 | 1992-05-26 | Bayer Aktiengesellschaft | Preparation of pharmaceutical or cosmetic dispersions |
| US4996004A (en) * | 1982-08-14 | 1991-02-26 | Bayer Aktiengesellschaft | Preparation of pharmaceutical or cosmetic dispersions |
| US4454113A (en) * | 1982-09-21 | 1984-06-12 | Scm Corporation | Stabilization of oil and water emulsions using polyglycerol esters of fatty acids |
| US4608057A (en) * | 1985-06-03 | 1986-08-26 | Texaco Inc. | Clear stable motor fuel composition |
| US5059347A (en) * | 1989-03-17 | 1991-10-22 | Ciba-Geigy Corporation | Aqueous antioxident emulsions |
| US5192462A (en) * | 1989-03-21 | 1993-03-09 | Croda Inc. | Thickening agents for topical preparations |
| EP0399377A1 (en) * | 1989-05-19 | 1990-11-28 | Nihon Parkerizing Co., Ltd. | Cold rolling oil for steel sheet |
| WO2005059042A3 (en) * | 2003-12-17 | 2005-11-03 | Ici Plc | Surfactant |
| US20070299228A1 (en) * | 2003-12-17 | 2007-12-27 | Imperial Chemical Industries Plc | Surfactant |
| US8883945B2 (en) | 2003-12-17 | 2014-11-11 | Croda International Plc | Surfactant |
| CN101448873B (en) * | 2006-05-19 | 2012-07-18 | 陶氏康宁东丽株式会社 | Polyether and method for producing the same |
| US11547137B2 (en) * | 2015-03-10 | 2023-01-10 | Givaudan Sa | Topical flavouring compositions comprising oleic acid and sodium oleate |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS539597B2 (en) | 1978-04-06 |
| JPS5118989A (en) | 1976-02-14 |
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